Tetrahydrofuran → Tris(4-ethynylphenyl)amine

HRID 1840695노트

반응식

HRID 1840695 반응식
O1CCCC1.C[Si]([C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C:31]2[CH:36]=[CH:35][C:34]([C:37]#[C:38][Si](C)(C)C)=[CH:33][CH:32]=2)[C:19]2[CH:24]=[CH:23][C:22]([C:25]#[C:26][Si](C)(C)C)=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)(C)C.[F-].[K+]>CO>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([N:18]([C:15]2[CH:14]=[CH:13][C:12]([C:11]#[CH:10])=[CH:17][CH:16]=2)[C:31]2[CH:36]=[CH:35][C:34]([C:37]#[CH:38])=[CH:33][CH:32]=2)=[CH:24][CH:23]=1)#[CH:26]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 522689Potassium FluorideHCID 23443707Tris(4-((trimethylsilyl)ethynyl)phenyl)amine

생성물 1

HCID 23443705Tris(4-ethynylphenyl)amine수율 75%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

To a mixture of 180 ml of tetrahydrofuran (THF) and 240 ml of methanol were added 13.84 g (0.026 mol) of tri(4-trimethylsilylethynylphenyl)amine and 4.53 g (0.078 mol) of potassium fluoride. The reaction mixture was heated at 50° C. for 5 h, cooled down to room temperature, and solvent was removed under the reduced pressure. The residue was extracted with ether and the ether layer was washed with distilled water. The washed ether layer was concentrated to give crude product. The crude product was purified by column chromatography on silica gel by eluting with hexane to give 6.182 g (75%) of tri(4-ethynylphenyl)amine of which NMR spectrum was shown in FIG. 9 and mp was 115° C.

후처리

  1. temperaturecooled down to room temperature
  2. customsolvent was removed under the reduced pressure
  3. extractionThe residue was extracted with ether
  4. washthe ether layer was washed with distilled water
  5. concentrationThe washed ether layer was concentrated
  6. customto give crude product
  7. customThe crude product was purified by column chromatography on silica gel
  8. washby eluting with hexane

출처 및 근거

ORD 기록
ord-571735d7247149858c6a591f017d96ed
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06682782B2

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